Co-founder Sam DeBrule of Heyday shares how they built an email list to 50k subscribers
Heyday co-founder tells us how they got early traction
Introducing Sam DeBrule, co-founder of Heyday
Heyday raised a $6.5M seed led by Spark Capital. I had a great conversation with Sam and he talked about some of their successes, failures, and experiments along their journey.
Sneak peek…
Some of the things we talk about:
How they built a waitlist of 50,000 people
Pivoting from Journal to now Heyday
Content instead of SEO
Hacking Substack for viral growth
Web clippers and other growth tricks
Can you tell us about Heyday and what you've been building the last few years?
Heyday is an AI-powered research assistant that resurfaces content you forgot about with enhanced search results, article overlays, and a knowledge base that fills itself.
So when you’re on the internet Googling or reading articles, we will inject content that you had seen previously within that flow.
How did that get started?
My co-founder Samiur and I were building a separate product called Journal in the productivity knowledge management space.
It was a far worse, less undifferentiated, less useful, less beautiful version of Notion. After a couple of years of pushing a boulder up hill, we realized that user traction feedback wasn't where we wanted it to be.
We were crazy enough to keep pushing and doing the startup thing, and the foundation of Heyday was from the insights and customer feedback when we were building Journal.
How long were you hacking on Journal before Heyday?
We were working on Journal for close to four years. It just wasn't resonating.
We had built a waitlist of 50,000 people. We were able to get those people into the top of the funnel, but they weren’t becoming paying customers.
So that was what eventually got us to the place of, “hey, we really need to make major changes. We need to work on something completely different.”
How did you build that email list to 50,000?
* TACTICAL CONTENT
We built up that email list primarily through content. We had built a really large publication on Medium.com called “Noteworthy.”
At its height, it grew to nearly a million unique visitors per month.
That publication was basically aggregated guest posts from different people on the platform who were writing and bragging about tech and productivity.
And the way that Medium works is when someone adds a post to your publication you get edit access over it.
So our pitch to writers on the platform was:
“Hey, if you submit your posts or publication, we will help you get more distribution via our email lists.”
The main incentive for these writers was getting their writing seen by others. And in exchange for that, we would add a call-to-action at the bottom of of the posts that pointed people to Journal.
One of the main interaction points with journal was a Web Clipper.
We would say “save this post in Journal” and when people clicked on that it would take them to the Journal landing page where they would learn about the product, and then they would sign up to the waitlist from there.
When did the light bulb go off in your head where you're like, “okay, we're clearly onto something here.”
We were fresh off of defeat of working on Journal.
Our number one marching order was no matter what, what we're building must be differentiated.
It can't be derivative of what is already existing in the market, and we were okay with it being polarizing.
INSIGHT #1
The initial thing that got us excited was when we talked about Heyday, instead of getting lukewarm responses from everyone, we got some people saying, “I'm not at all interested in this at all.”
And then on the other side of the spectrum, there were these people who were super excited about the idea of this brain that's working in the background for them.
So it was the initial feedback that got us excited—just that there were these two polar opposites in reaction when we presented the idea to people.
INSIGHT #2
We also removed the waitlist and awesome things started happening.
A writer for Fast Company then reached out and I was said, “Hey guys, is it cool if I write about this product?”
The same thing happened with a writer for Morning Brew, and she wrote about us and included us in the newsletter—that was incredible.
We were able to get people into the product and convert free users into paid users at a rate of about 10%, which is really high for the nature of the product that we're working on.
What were some early experiments that helped you get off the ground?
EXPERIMENT #1 - BUILDING A VETTED WAITLIST
We had a waitlist. It was one of the main ones that we ran and was informed by our initial onboarding experience process.
After talking to a lot of customers, we were able to identify certain traits that lead someone to be more likely to convert to a customer than others.
EXPERIMENT #2 - SPONSORING SUBSTACK NEWSLETTERS
We noticed that if you subscribed to five plus Substacks, then that was a sign of someone who's doing a lot of research, and someone who would get make the most value out of Heyday.
So, we just started ideating: “okay, if the people who really want to get into the product are hanging out on Twitter and Substack, how might we bring more of those people in?”
So one of the experiments we ran was sponsoring Substack writers.
By sponsoring their newsletters directly, they would place an ad about Heyday within their newsletter, and we would pay them in exchange for it. Then that would drive highly qualified traffic and users to sign up for our product.
EXPERIMENT #3 - FACEBOOK ADS
We ran and continue to run experiments with more scaled channels like Facebook ads. Facebook is great at generating demand.
We've seen a far lower cost per conversion and cost for acquiring a new trial, and that's because we are able to get people excited about Heyday on Facebook, and that it solves information overload while they’re scrolling through their feed.
FAILED EXPERIMENT - GOOGLE ADS
It may not come as a surprise that not many people are searching for AI powered research assistants on Google.
Search ads on Google are really powerful for capturing existing intent versus generating demand.
But there's very little search intent for this, so it ended up being very expensive for us to acquire new trial users from Google.
What kinds of demand generating channels and platforms are intriguing to you right now?
If we're talking about massively scaled platforms, the elephant in the room is TikTok.
What advice would you give to first time founders or folks just looking to get their project or startup off the ground?
#1 - You have to have a lot of confidence in yourself. I think when you're working on a company, someone who is a founder, someone who decides to build a company and stick at it for a while, and are stubborn person, you want to believe that you can do it.
#2 - Be vulnerable. It's hard to be vulnerable. It's hard to open up to the outside world, especially when things aren't going well. And you're only seeing success stories on Twitter and things like that. It's okay to be vulnerable and to really show the good, bad, and ugly.
#3 - Get outside of your own head. Talk to other people who have already solved a specific challenge that you're overcoming, whether it’s growth or recruiting. Talk to other founders who are succeeding, who are in the hard parts of the process themselves.
So much value will come from overcoming these obstacles that you're trying to get past, and having the mental and emotional fortitude that you need to keep pushing forward is powerful.
The final word
I think there is so much value out of not just sharing the wins, but sharing the challenges that you face, and the ugly realities of your product, of the processes that are broken within your company, because that gets people excited and is useful for others who are going through a similar process.
— Sam DeBrule
Thanks for reading!
You can find Sam and Heyday at these links:
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